Kinetic resolution of racemic 2-substituted 1,2-dihydroquinolines via asymmetric Cu-catalyzed borylation.

ABSTRACT: A highly efficient kinetic resolution of racemic 2-substituted 1,2-dihydroquinolines via asymmetric Cu-catalyzed borylation has been realized for the first time. Under mild conditions, a variety of chiral 3-boryl-1,2,3,4-tetrahydroquinolines containing two vicinal stereogenic centers as well as the recovered 2-substituted 1,2-dihydroquinolines were afforded after 30 minutes in high yields with up to 99% ee (dr > 99 : 1) and over 98% ee values, respectively, corresponding to kinetic selectivity factors of up to 569. Moreover, this protocol was successfully applied to the asymmetric synthesis of a selective estrogen receptor modulator.

SUBMITTER: Kong D 

PROVIDER: S-EPMC5590099 | biostudies-literature |

REPOSITORIES: biostudies-literature